Vacation rentals in Peekskill

4.91 out of 5 average rating, 232 reviews

Apartment in Philipstown

Foxglove Farm

Peace and tranquility await you at the end of this private road surrounded by forest. My home is a log cabin with a private apartment on the lower level, which includes a patio as well as use of other outdoor spaces. There is a fire pit just past your patio and a short path will put you on the Appalachian Trail. As an herbalist and ethnobotanist, plants are my love and my livelihood. They are an integral part of my life and my home. I welcome you to stroll through the many gardens and paths.

4.99 out of 5 average rating, 196 reviews

Cottage in Cortlandt

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

4.94 out of 5 average rating, 140 reviews

Cottage in Cold Spring

Cheerful Private 3 Bedroom Cottage in Cold Spring

Relax with friends & family at this peaceful forrest cottage, just 7-minutes outside of The Historic Village of Cold Spring on a beautiful, quiet country road. Much bigger on the inside than it looks, this place has what you need: fresh linens, full kitchen, wifi, streaming tvs and plenty of great books to read. There is a trampoline in the backyard & patio lights for Spring/Summer/Fall nights dining outside. Rent alone or pair with my cottage next door: Peaceful Yellow Door Cottage on Airbnb.

4.95 out of 5 average rating, 135 reviews

Apartment in Ossining

Gorgeous 1 BR w/High End Finishes, Heated BA Floor

Unwind at this peaceful retreat a short walk from downtown Ossining and Hudson River front parks. Designed with end to end comfort, beautifully decorated, and featuring a gorgeous open kitchen and entertaining room, in this space you can relax and step away from it all. Highlights include: 2nd floor walk-up High End Appliances and all Finishes Heated bathroom floors Contactless entry Off-street parking 1/2 block from multiple parks Weekly discount available Come stay here! You’ll love it

4.8 out of 5 average rating, 168 reviews

Apartment in Peekskill

Little haven by the woods

This is a walk-out basement with two private entrances, and it’s own private outside area. The patio has comfy furniture with a bbq. The kitchen is small, yet efficient with large windows. The bedroom is cozy and comfy with a large smart tv on the wall. The bedroom has a 3/4 wall dividing it from the rest of the apt, but no actual door. So it could be considered a “studio”. We are steps from the trail heads into Blue Mt park. We’re also walking distance to the metro north & downtown.

Guest suite in Croton-on-Hudson

4.92 out of 5 average rating, 134 reviews

The Bluestone - Spacious 2 bedroom w/central air

Come stay with us! You will have the entire first floor to yourself but we will be right upstairs if you should need us! Access to tree lined back yard with fire pit. Close to metro north train to NYC. Minutes to kayaking, hiking, restaurants, cafes & historical sites. Please note: Drive, walkway and entrance accessible to full size wheelchair (see photos) however the bathroom is not accessible to a wheelchair. Guest must have ability to enter and maneuver the bathroom on thier own.

4.9 out of 5 average rating, 190 reviews

Home in Peekskill

The Peekskill RiverView House

The Peekskill RiverView House A fully renovated dream house overlooking the historic Peekskill Bay. This 3 bedroom 3.5 bath designer house is a 5 minute walk to the train station as well as the historic downtown. It’s truly the gateway to the Hudson Valley along with having the walkable access to culture, hiking, biking, culinary, spa, and entertainment activities within City limits. Expansive decks on all 3 floors with spectacular Hudson River views from every room.

4.99 out of 5 average rating, 311 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

4.96 out of 5 average rating, 111 reviews

Guest suite in Cornwall

Studio in Cornwall

Located near the village, hiking trails, Jones Farm, Hudson River, Woodbury Commons, West Point and more. The studio is ground level with a private entrance. The kitchenette incudes a convection toaster oven, a hot plate cooktop with pots/pans, light kitchenware, coffee maker, & fridge. Also provided: TV, Roku stick, Wi-Fi, AC/electric heat. (No cable) This is our home. The use of illicit drugs, smoking and excessive alcohol is prohibited.

4.96 out of 5 average rating, 165 reviews

Cottage in Putnam Valley

Private Lake House 1 Hour to NYC & Near Westpoint

Escape to this private lake cottage. Just 1h drive from NYC, near lots of skiing & hiking Thunder Ridge (30mi) Mt Peter (30mi) Victor Constant (20mi) Campgaw Mountain (40mi) Enjoy panoramic lake views, 86in TV, ample board games, 5-jet shower, and indoor jetted Jacuzzi tub. Short drive to Bear Mountain & West Point. Legoland is 45 min away Pets are welcome! WiFi is extremely fast and we have free electric car charging

4.98 out of 5 average rating, 125 reviews

Loft in Mountainville

Lovely, Quiet and Very Private! Entire Loft!

Nestled in the mountains is a peaceful place to lay your head. Just a stones throw from vineyards, brewery's and some of the best views and attractions the Hudson Valley has to offer. Here you'll find a private & secluded bedroom and bathroom fit for 2. A small "kitchenette" is avaliable for use as well as an outdoor seating area with fireplace. Free parking in designated spot. Waterfall is a short hike away.

4.91 out of 5 average rating, 204 reviews

Cottage in Mohegan Lake

The Pearl of Westchester

Welcome to the Paradise! This Pearl of Westchester are nested with a Main house on private 2 acres of direct waterfront estate. Offering a private dock and beach in a flawless natural paradise. Enjoy swimming, fishing, boating or barbecuing on a private porch. Hiking in walking distance Located less than an hour away from NYC. Peekskill Metro North is 15 min away.

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Popular amenities for Peekskill vacation rentals

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Laptop-friendly workspace

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Other great vacation rentals in Peekskill

4.98 out of 5 average rating, 100 reviews

Home in Highland Falls

Bear Mountain, Westpoint, & Hikers Retreat

MitchellRating, 5 stars3 weeks ago

Great place to stay for a relaxing weekend in the Hudson valley. Was extremely close to plenty of restaurants and things to see. I would definitely stay here again if I was coming back to the area.

4.93 out of 5 average rating, 219 reviews

Home in Wappingers Falls

Tranquil Tree-House on the beautiful Hudson River

MatthewRating, 5 stars2 weeks ago

A truly magical escape. This sacred treehouse was absolutely perfect - peaceful, stunning, and deeply rejuvenating. Rob and Roberta were the kindest, most thoughtful hosts I’ve ever encountered on Airbnb. Their warmth made the experience even more special. From sunbathing on the rocks and meditating in the grass, to yoga overlooking the water and cooking local organic meals - every moment was magic. Already planning my return. Thank you, Roberta and Rob!!

Guest suite in Fort Montgomery

4.96 out of 5 average rating, 112 reviews

West Point/Bear Mountain/Hudson Valley Getaway

Shara-SueRating, 5 stars2 weeks ago

Lovely space with nice proximity to West Point -- the reason for the visit! The place is just as pictured and described. The highlights were the extremely comfortable beds and couches, the great indoor & outdoor space, and the spacious & stocked bathroom; it was just perfect for what we needed and wanted. Thanks so much! :)

Apartment in Croton-on-Hudson

4.98 out of 5 average rating, 343 reviews

Luxury 2bd⭐Comfort+Style⭐

AndreasRating, 5 stars2 weeks ago

Maria was a great host, super helpful and sweet. Our family really enjoyed staying here!

4.87 out of 5 average rating, 415 reviews

Apartment in Cold Spring

Idyllic! Just steps from Main Street!

GlennRating, 5 stars1 week ago

I really liked that we had a personal parking spot, and the location is awesome. We very much enjoyed the stay !!

Farm stay in Fort Montgomery

4.98 out of 5 average rating, 194 reviews

Secluded overlook cottage near West Point

Alec & LauraRating, 5 stars1 month ago

We loved staying here, and our son loved visiting the horses, and the chickens in the barn. And we saw wild turkeys and deer roaming the property. And it was great to see the horses run on our way out! There are also lots of little streams and tiny waterfalls we enjoyed checking out. And the farm fresh eggs were a lovely and much appreciate bonus!

4.84 out of 5 average rating, 310 reviews

Apartment in Newburgh

Unwind in a Bespoke Downtown Studio W Laundry

DaniyalRating, 5 stars2 weeks ago

Great place! Needed a last minute space and was approved very quickly. Very responsive and helpful, clean and tidy space with everything you need. Thank you for a wonderful stay!